Stereoselective synthesis of 2-(α-hydroxyalkyl)benzimidazoles

Chiral Heterocycles by Iminium Ion Cyclization

“…Consequently, a mixture of isomers was observed. 106 Oxazolidines incorporated in other bicyclic or more complex structures were obtained through cyclization onto iminium ions produced with various methods involving aminonitrile displacement, 107 oxidation of the benzylic position, 108 azaelectrocyclization to dihydropyridine, 109 amine-aldehyde condensation, 110 and N-oxide deprotonation. 111 The configuration of the new chiral center proved to be highly structuredependent.…”

Asymmetric Diels–Alder reaction involving chiral benzimidazoles as organocatalysts

“…The benzimdazoles are predominantly basic compounds having ability to accept a proton. We have employed heterocyclic chiral bases namely ( S )‐(−)‐2‐(α‐hydroxyethyl)‐benzimidazole18, 19 ( 1 ) and ( S)‐ (+)‐2‐(α‐hydroxybenzyl)‐benzimidazole20, 21 ( 2 ) for the reaction between anthrone and various maleimides. The selection of both chiral bases was driven on the basis of several factors.…”

Enantioselective Benzoylation of α-Amino Esters Using (S)-1-Benzoyl-2- (α-acetoxyethyl)benzimidazole, a Chiral Benzimidazolide

“…Condensation of o -phenylene diamine with ( S )-lactic acid is reported to afford ( S )-2-(α-hydroxyethyl)benzimidazole ( 1 ) …”